Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025858/at2303sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025858/at2303Isup2.hkl |
CCDC reference: 628843
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- R factor = 0.021
- wR factor = 0.048
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT128_ALERT_4_C Non-standard setting of Space group Pc .... Pn PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.20 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.39 Ratio
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.36 From the CIF: _reflns_number_total 2934 Count of symmetry unique reflns 2017 Completeness (_total/calc) 145.46% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 917 Fraction of Friedel pairs measured 0.455 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
1-(2-Pyridyl)piperazine (2 mmol), carbondisulfide (2 mmol) and diphenyltin dichloride (1 mmol) were suspended in dry methanol (150 ml) in a two necked round bottom flask. The mixture was stirred at room temperature for 24 h. Solid product obtained was filtered off and recrystallized from DMSO to obtain colourless crystals suitable for X-ray analysis (yield 65%; m.p. 414–416 K).
H atoms were included in calculated positions using the riding method, with C—H = 0.95 - 0.98 Å and Ueq values 1.2 times those of the parent atoms (1.5 times those of the methyl C atoms).
There have been several reports dealing with the impact of organotin chemistry in the biosphere (Gielen, 1994; Ng et al., 1991). Exploration of the structural-activity relationships of such systems has led to numerous reports in recent years (Gielen, 1994; Selvaratnam et al., 1994; McManus et al., 1994). Organotin compounds are of current interest due to their dramatic increase of industrial, agricultural and biological applications (Xie et al., 1996; Nath et al., 2001). The studies of organotin and biologically important ligands have gained importance due to potential pharmaceutical applications of organotin compounds (Anderson et al., 1984). We report here the crystal structure of the title compound (I) as a continuation of our efforts in the synthesis and structural characterization of organotin(IV) complexes (Shahzadi et al., 2006) (Fig 1).
The Sn atom is bonded to two phenyls, two DMSO groups and two chlorides forming a distorted octahedral geometry. The Sn—C distances lie in the range 2.139 (4) - 2.156 (4) Å which is longer than Sn—C distance reported earlier (Shahzadi et al., 2006). The C1—Sn1—C7 and O1—Sn1—Cl2 angles are 172.19 (3) and 170.97 (6)°, respectively (Table 1). The molecules are linked by C—H···O and C—H···Cl hydrogen bonds (Table 1, Fig.2) and C—H···π interactions between H11—Cg1 (symmetry equivalent -1 + x, y, z) and H13A and Cg2 (symmetry equivalent 1/2 + x, 1 - y, -1/2 + z) with distances of 2.8 and 2.75, where Cg1 and Cg2 are the phenyl rings C1—C6 and C7—C12, respectively.
For related literature, see: Anderson et al. (1984); Gielen (1994); McManus et al. (1994); Nath et al. (2001); Ng et al. (1991); Selvaratnam et al. (1994); Shahzadi et al. (2006); Xie et al. (1996).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL and PLATON (Spek 2003).
Fig. 1. Structure of (I) with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. Packing of (I) viewed down the b axis showing the hydrogen bonding interactions with dotted lines.. |
[Sn(C6H5)2Cl2(C2H6OS)2] | F(000) = 500 |
Mr = 500.05 | Dx = 1.680 Mg m−3 |
Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yac | Cell parameters from 3405 reflections |
a = 9.8877 (8) Å | θ = 2.5–26.4° |
b = 7.9766 (6) Å | µ = 1.78 mm−1 |
c = 12.588 (1) Å | T = 100 K |
β = 95.506 (1)° | Rectangular, colourless |
V = 988.24 (13) Å3 | 0.40 × 0.20 × 0.20 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 2934 independent reflections |
Radiation source: fine-focus sealed tube | 2884 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −12→8 |
Tmin = 0.536, Tmax = 0.717 | k = −9→9 |
5514 measured reflections | l = −15→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.021 | H-atom parameters constrained |
wR(F2) = 0.048 | w = 1/[σ2(Fo2) + (0.0248P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2934 reflections | Δρmax = 0.63 e Å−3 |
212 parameters | Δρmin = −0.50 e Å−3 |
2 restraints | Absolute structure: Flack (1983), with 917 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.024 (17) |
[Sn(C6H5)2Cl2(C2H6OS)2] | V = 988.24 (13) Å3 |
Mr = 500.05 | Z = 2 |
Monoclinic, Pn | Mo Kα radiation |
a = 9.8877 (8) Å | µ = 1.78 mm−1 |
b = 7.9766 (6) Å | T = 100 K |
c = 12.588 (1) Å | 0.40 × 0.20 × 0.20 mm |
β = 95.506 (1)° |
Bruker SMART CCD area-detector diffractometer | 2934 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2884 reflections with I > 2σ(I) |
Tmin = 0.536, Tmax = 0.717 | Rint = 0.020 |
5514 measured reflections |
R[F2 > 2σ(F2)] = 0.021 | H-atom parameters constrained |
wR(F2) = 0.048 | Δρmax = 0.63 e Å−3 |
S = 1.05 | Δρmin = −0.50 e Å−3 |
2934 reflections | Absolute structure: Flack (1983), with 917 Freidel pairs |
212 parameters | Absolute structure parameter: 0.024 (17) |
2 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.87116 (2) | 0.73205 (2) | 0.06392 (2) | 0.01157 (6) | |
S1 | 1.06401 (9) | 0.52499 (11) | −0.09835 (7) | 0.01579 (19) | |
S2 | 1.02952 (11) | 0.42840 (11) | 0.23125 (7) | 0.0206 (2) | |
Cl1 | 0.77624 (10) | 0.98627 (11) | −0.02938 (7) | 0.01949 (19) | |
Cl2 | 0.82060 (10) | 0.81165 (12) | 0.24691 (7) | 0.0198 (2) | |
O1 | 0.9310 (2) | 0.6217 (3) | −0.09105 (19) | 0.0155 (5) | |
O2 | 0.9624 (3) | 0.4828 (3) | 0.1231 (2) | 0.0210 (6) | |
C1 | 1.0711 (4) | 0.8424 (4) | 0.0825 (3) | 0.0127 (7) | |
C2 | 1.1228 (4) | 0.9177 (4) | −0.0049 (3) | 0.0159 (8) | |
H2 | 1.0705 | 0.9166 | −0.0722 | 0.019* | |
C3 | 1.2497 (4) | 0.9946 (4) | 0.0047 (3) | 0.0189 (8) | |
H3 | 1.2844 | 1.0428 | −0.0562 | 0.023* | |
C4 | 1.3253 (4) | 1.0006 (4) | 0.1028 (3) | 0.0189 (8) | |
H4 | 1.4115 | 1.0541 | 0.1096 | 0.023* | |
C5 | 1.2750 (4) | 0.9282 (4) | 0.1915 (3) | 0.0167 (8) | |
H5 | 1.3270 | 0.9327 | 0.2590 | 0.020* | |
C6 | 1.1492 (4) | 0.8494 (4) | 0.1819 (3) | 0.0149 (7) | |
H6 | 1.1156 | 0.8000 | 0.2428 | 0.018* | |
C7 | 0.6846 (4) | 0.5975 (4) | 0.0322 (3) | 0.0147 (7) | |
C8 | 0.6804 (4) | 0.4271 (4) | 0.0050 (3) | 0.0154 (7) | |
H8 | 0.7629 | 0.3683 | −0.0009 | 0.019* | |
C9 | 0.5576 (4) | 0.3430 (5) | −0.0136 (3) | 0.0175 (8) | |
H9 | 0.5566 | 0.2275 | −0.0321 | 0.021* | |
C10 | 0.4357 (4) | 0.4273 (4) | −0.0052 (3) | 0.0166 (8) | |
H10 | 0.3515 | 0.3700 | −0.0180 | 0.020* | |
C11 | 0.4387 (4) | 0.5969 (5) | 0.0224 (3) | 0.0190 (8) | |
H11 | 0.3563 | 0.6555 | 0.0291 | 0.023* | |
C12 | 0.5621 (4) | 0.6799 (5) | 0.0400 (3) | 0.0168 (8) | |
H12 | 0.5629 | 0.7957 | 0.0578 | 0.020* | |
C13 | 1.1218 (4) | 0.5947 (5) | −0.2208 (3) | 0.0245 (9) | |
H13A | 1.0480 | 0.5843 | −0.2782 | 0.037* | |
H13B | 1.1990 | 0.5258 | −0.2377 | 0.037* | |
H13C | 1.1502 | 0.7122 | −0.2139 | 0.037* | |
C14 | 1.0108 (4) | 0.3205 (5) | −0.1386 (3) | 0.0228 (8) | |
H14A | 0.9738 | 0.2631 | −0.0789 | 0.034* | |
H14B | 1.0886 | 0.2573 | −0.1603 | 0.034* | |
H14C | 0.9405 | 0.3281 | −0.1989 | 0.034* | |
C15 | 1.2005 (5) | 0.3876 (6) | 0.2057 (4) | 0.0369 (11) | |
H15A | 1.2014 | 0.3062 | 0.1474 | 0.055* | |
H15B | 1.2508 | 0.3421 | 0.2701 | 0.055* | |
H15C | 1.2433 | 0.4921 | 0.1854 | 0.055* | |
C16 | 0.9765 (6) | 0.2180 (5) | 0.2451 (5) | 0.0407 (13) | |
H16A | 0.8812 | 0.2161 | 0.2604 | 0.061* | |
H16B | 1.0329 | 0.1647 | 0.3039 | 0.061* | |
H16C | 0.9861 | 0.1569 | 0.1787 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01164 (11) | 0.01114 (10) | 0.01229 (10) | 0.00108 (13) | 0.00299 (7) | −0.00024 (13) |
S1 | 0.0119 (4) | 0.0192 (4) | 0.0167 (4) | 0.0013 (4) | 0.0036 (3) | −0.0044 (3) |
S2 | 0.0318 (6) | 0.0153 (5) | 0.0153 (4) | 0.0075 (4) | 0.0047 (4) | 0.0014 (3) |
Cl1 | 0.0171 (5) | 0.0160 (4) | 0.0259 (4) | 0.0041 (3) | 0.0045 (4) | 0.0067 (3) |
Cl2 | 0.0225 (5) | 0.0229 (5) | 0.0153 (4) | −0.0040 (4) | 0.0088 (4) | −0.0041 (3) |
O1 | 0.0127 (13) | 0.0181 (13) | 0.0159 (12) | 0.0018 (10) | 0.0027 (10) | −0.0040 (10) |
O2 | 0.0231 (16) | 0.0156 (13) | 0.0231 (14) | 0.0049 (12) | −0.0045 (11) | 0.0003 (10) |
C1 | 0.0123 (18) | 0.0096 (16) | 0.0163 (17) | 0.0028 (14) | 0.0022 (14) | −0.0031 (13) |
C2 | 0.018 (2) | 0.0145 (18) | 0.0164 (18) | 0.0027 (15) | 0.0050 (15) | −0.0024 (14) |
C3 | 0.026 (2) | 0.0113 (17) | 0.0206 (18) | −0.0011 (15) | 0.0098 (15) | 0.0023 (14) |
C4 | 0.015 (2) | 0.0116 (17) | 0.030 (2) | −0.0018 (15) | 0.0049 (16) | −0.0027 (15) |
C5 | 0.016 (2) | 0.0133 (17) | 0.0198 (18) | 0.0054 (15) | −0.0026 (15) | −0.0022 (14) |
C6 | 0.0189 (19) | 0.0115 (17) | 0.0147 (17) | 0.0029 (14) | 0.0042 (14) | −0.0022 (13) |
C7 | 0.0170 (19) | 0.0164 (18) | 0.0113 (16) | 0.0010 (15) | 0.0050 (14) | 0.0024 (13) |
C8 | 0.0149 (19) | 0.0170 (18) | 0.0147 (17) | 0.0025 (15) | 0.0034 (14) | 0.0019 (14) |
C9 | 0.020 (2) | 0.0125 (18) | 0.0206 (18) | 0.0025 (15) | 0.0033 (16) | 0.0005 (15) |
C10 | 0.0115 (19) | 0.0183 (18) | 0.0205 (18) | −0.0047 (14) | 0.0041 (15) | −0.0003 (14) |
C11 | 0.0122 (19) | 0.0211 (19) | 0.0242 (19) | 0.0041 (15) | 0.0036 (15) | 0.0018 (15) |
C12 | 0.016 (2) | 0.0148 (18) | 0.0201 (18) | 0.0009 (15) | 0.0039 (15) | −0.0001 (14) |
C13 | 0.027 (2) | 0.024 (2) | 0.025 (2) | −0.0026 (17) | 0.0149 (18) | −0.0065 (16) |
C14 | 0.021 (2) | 0.0165 (19) | 0.032 (2) | 0.0020 (16) | 0.0081 (17) | 0.0010 (16) |
C15 | 0.020 (2) | 0.025 (2) | 0.061 (3) | 0.0036 (19) | −0.015 (2) | 0.002 (2) |
C16 | 0.038 (3) | 0.020 (2) | 0.069 (4) | 0.007 (2) | 0.031 (3) | 0.018 (2) |
Sn1—C7 | 2.139 (4) | C7—C12 | 1.390 (5) |
Sn1—C1 | 2.156 (4) | C7—C8 | 1.402 (5) |
Sn1—O1 | 2.270 (2) | C8—C9 | 1.387 (5) |
Sn1—O2 | 2.279 (2) | C8—H8 | 0.9500 |
Sn1—Cl1 | 2.4821 (9) | C9—C10 | 1.393 (5) |
Sn1—Cl2 | 2.4860 (9) | C9—H9 | 0.9500 |
S1—O1 | 1.535 (3) | C10—C11 | 1.397 (5) |
S1—C14 | 1.773 (4) | C10—H10 | 0.9500 |
S1—C13 | 1.784 (4) | C11—C12 | 1.387 (5) |
S2—O2 | 1.519 (3) | C11—H11 | 0.9500 |
S2—C16 | 1.772 (4) | C12—H12 | 0.9500 |
S2—C15 | 1.781 (5) | C13—H13A | 0.9800 |
C1—C2 | 1.393 (5) | C13—H13B | 0.9800 |
C1—C6 | 1.407 (5) | C13—H13C | 0.9800 |
C2—C3 | 1.391 (5) | C14—H14A | 0.9800 |
C2—H2 | 0.9500 | C14—H14B | 0.9800 |
C3—C4 | 1.381 (6) | C14—H14C | 0.9800 |
C3—H3 | 0.9500 | C15—H15A | 0.9800 |
C4—C5 | 1.391 (5) | C15—H15B | 0.9800 |
C4—H4 | 0.9500 | C15—H15C | 0.9800 |
C5—C6 | 1.389 (5) | C16—H16A | 0.9800 |
C5—H5 | 0.9500 | C16—H16B | 0.9800 |
C6—H6 | 0.9500 | C16—H16C | 0.9800 |
C7—Sn1—C1 | 172.19 (13) | C12—C7—Sn1 | 119.4 (3) |
C7—Sn1—O1 | 86.36 (11) | C8—C7—Sn1 | 122.5 (3) |
C1—Sn1—O1 | 86.54 (11) | C9—C8—C7 | 121.0 (4) |
C7—Sn1—O2 | 86.02 (12) | C9—C8—H8 | 119.5 |
C1—Sn1—O2 | 89.46 (11) | C7—C8—H8 | 119.5 |
O1—Sn1—O2 | 79.35 (9) | C8—C9—C10 | 120.2 (3) |
C7—Sn1—Cl1 | 92.38 (10) | C8—C9—H9 | 119.9 |
C1—Sn1—Cl1 | 91.08 (9) | C10—C9—H9 | 119.9 |
O1—Sn1—Cl1 | 91.61 (6) | C9—C10—C11 | 119.2 (4) |
O2—Sn1—Cl1 | 170.89 (7) | C9—C10—H10 | 120.4 |
C7—Sn1—Cl2 | 93.11 (10) | C11—C10—H10 | 120.4 |
C1—Sn1—Cl2 | 93.38 (9) | C12—C11—C10 | 120.0 (4) |
O1—Sn1—Cl2 | 170.97 (6) | C12—C11—H11 | 120.0 |
O2—Sn1—Cl2 | 91.62 (7) | C10—C11—H11 | 120.0 |
Cl1—Sn1—Cl2 | 97.42 (3) | C11—C12—C7 | 121.5 (3) |
O1—S1—C14 | 104.30 (17) | C11—C12—H12 | 119.3 |
O1—S1—C13 | 104.04 (16) | C7—C12—H12 | 119.3 |
C14—S1—C13 | 98.65 (19) | S1—C13—H13A | 109.5 |
O2—S2—C16 | 104.5 (2) | S1—C13—H13B | 109.5 |
O2—S2—C15 | 103.3 (2) | H13A—C13—H13B | 109.5 |
C16—S2—C15 | 98.0 (2) | S1—C13—H13C | 109.5 |
S1—O1—Sn1 | 122.81 (13) | H13A—C13—H13C | 109.5 |
S2—O2—Sn1 | 131.88 (15) | H13B—C13—H13C | 109.5 |
C2—C1—C6 | 118.2 (3) | S1—C14—H14A | 109.5 |
C2—C1—Sn1 | 119.5 (3) | S1—C14—H14B | 109.5 |
C6—C1—Sn1 | 122.1 (3) | H14A—C14—H14B | 109.5 |
C3—C2—C1 | 121.2 (3) | S1—C14—H14C | 109.5 |
C3—C2—H2 | 119.4 | H14A—C14—H14C | 109.5 |
C1—C2—H2 | 119.4 | H14B—C14—H14C | 109.5 |
C4—C3—C2 | 119.9 (3) | S2—C15—H15A | 109.5 |
C4—C3—H3 | 120.0 | S2—C15—H15B | 109.5 |
C2—C3—H3 | 120.0 | H15A—C15—H15B | 109.5 |
C3—C4—C5 | 120.0 (4) | S2—C15—H15C | 109.5 |
C3—C4—H4 | 120.0 | H15A—C15—H15C | 109.5 |
C5—C4—H4 | 120.0 | H15B—C15—H15C | 109.5 |
C6—C5—C4 | 120.2 (3) | S2—C16—H16A | 109.5 |
C6—C5—H5 | 119.9 | S2—C16—H16B | 109.5 |
C4—C5—H5 | 119.9 | H16A—C16—H16B | 109.5 |
C5—C6—C1 | 120.4 (3) | S2—C16—H16C | 109.5 |
C5—C6—H6 | 119.8 | H16A—C16—H16C | 109.5 |
C1—C6—H6 | 119.8 | H16B—C16—H16C | 109.5 |
C12—C7—C8 | 118.1 (4) | ||
C14—S1—O1—Sn1 | 117.33 (19) | C1—C2—C3—C4 | −1.6 (5) |
C13—S1—O1—Sn1 | −139.74 (17) | C2—C3—C4—C5 | 0.7 (5) |
C7—Sn1—O1—S1 | −126.56 (18) | C3—C4—C5—C6 | 0.2 (5) |
C1—Sn1—O1—S1 | 50.17 (17) | C4—C5—C6—C1 | −0.2 (5) |
O2—Sn1—O1—S1 | −39.93 (16) | C2—C1—C6—C5 | −0.6 (5) |
Cl1—Sn1—O1—S1 | 141.16 (15) | Sn1—C1—C6—C5 | −177.1 (3) |
C16—S2—O2—Sn1 | 143.5 (2) | O1—Sn1—C7—C12 | −131.5 (3) |
C15—S2—O2—Sn1 | −114.4 (2) | O2—Sn1—C7—C12 | 148.9 (3) |
C7—Sn1—O2—S2 | −119.4 (2) | Cl1—Sn1—C7—C12 | −40.0 (3) |
C1—Sn1—O2—S2 | 67.0 (2) | Cl2—Sn1—C7—C12 | 57.5 (3) |
O1—Sn1—O2—S2 | 153.6 (2) | O1—Sn1—C7—C8 | 49.3 (3) |
Cl2—Sn1—O2—S2 | −26.4 (2) | O2—Sn1—C7—C8 | −30.2 (3) |
O1—Sn1—C1—C2 | 43.7 (3) | Cl1—Sn1—C7—C8 | 140.8 (3) |
O2—Sn1—C1—C2 | 123.1 (3) | Cl2—Sn1—C7—C8 | −121.6 (3) |
Cl1—Sn1—C1—C2 | −47.8 (3) | C12—C7—C8—C9 | −0.1 (5) |
Cl2—Sn1—C1—C2 | −145.3 (3) | Sn1—C7—C8—C9 | 179.1 (3) |
O1—Sn1—C1—C6 | −139.8 (3) | C7—C8—C9—C10 | −0.1 (5) |
O2—Sn1—C1—C6 | −60.5 (3) | C8—C9—C10—C11 | −0.2 (5) |
Cl1—Sn1—C1—C6 | 128.6 (3) | C9—C10—C11—C12 | 0.6 (6) |
Cl2—Sn1—C1—C6 | 31.1 (3) | C10—C11—C12—C7 | −0.8 (6) |
C6—C1—C2—C3 | 1.5 (5) | C8—C7—C12—C11 | 0.6 (5) |
Sn1—C1—C2—C3 | 178.1 (3) | Sn1—C7—C12—C11 | −178.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···O1i | 0.98 | 2.39 | 3.260 (5) | 148 |
C3—H3···Cl2ii | 0.95 | 2.79 | 3.721 (4) | 166 |
C14—H14B···Cl2iii | 0.98 | 2.73 | 3.663 (4) | 160 |
Symmetry codes: (i) x+1/2, −y+1, z+1/2; (ii) x+1/2, −y+2, z−1/2; (iii) x+1/2, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H5)2Cl2(C2H6OS)2] |
Mr | 500.05 |
Crystal system, space group | Monoclinic, Pn |
Temperature (K) | 100 |
a, b, c (Å) | 9.8877 (8), 7.9766 (6), 12.588 (1) |
β (°) | 95.506 (1) |
V (Å3) | 988.24 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.78 |
Crystal size (mm) | 0.40 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.536, 0.717 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5514, 2934, 2884 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.021, 0.048, 1.05 |
No. of reflections | 2934 |
No. of parameters | 212 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.63, −0.50 |
Absolute structure | Flack (1983), with 917 Freidel pairs |
Absolute structure parameter | 0.024 (17) |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL and PLATON (Spek 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···O1i | 0.98 | 2.39 | 3.260 (5) | 147.6 |
C3—H3···Cl2ii | 0.95 | 2.79 | 3.721 (4) | 166.3 |
C14—H14B···Cl2iii | 0.98 | 2.73 | 3.663 (4) | 159.6 |
Symmetry codes: (i) x+1/2, −y+1, z+1/2; (ii) x+1/2, −y+2, z−1/2; (iii) x+1/2, −y+1, z−1/2. |
There have been several reports dealing with the impact of organotin chemistry in the biosphere (Gielen, 1994; Ng et al., 1991). Exploration of the structural-activity relationships of such systems has led to numerous reports in recent years (Gielen, 1994; Selvaratnam et al., 1994; McManus et al., 1994). Organotin compounds are of current interest due to their dramatic increase of industrial, agricultural and biological applications (Xie et al., 1996; Nath et al., 2001). The studies of organotin and biologically important ligands have gained importance due to potential pharmaceutical applications of organotin compounds (Anderson et al., 1984). We report here the crystal structure of the title compound (I) as a continuation of our efforts in the synthesis and structural characterization of organotin(IV) complexes (Shahzadi et al., 2006) (Fig 1).
The Sn atom is bonded to two phenyls, two DMSO groups and two chlorides forming a distorted octahedral geometry. The Sn—C distances lie in the range 2.139 (4) - 2.156 (4) Å which is longer than Sn—C distance reported earlier (Shahzadi et al., 2006). The C1—Sn1—C7 and O1—Sn1—Cl2 angles are 172.19 (3) and 170.97 (6)°, respectively (Table 1). The molecules are linked by C—H···O and C—H···Cl hydrogen bonds (Table 1, Fig.2) and C—H···π interactions between H11—Cg1 (symmetry equivalent -1 + x, y, z) and H13A and Cg2 (symmetry equivalent 1/2 + x, 1 - y, -1/2 + z) with distances of 2.8 and 2.75, where Cg1 and Cg2 are the phenyl rings C1—C6 and C7—C12, respectively.